How to Help Your Remote Team Take More Risks

The key is helping team members to trust each other.

Munir Pathak
tryswirl
4 min readFeb 21, 2020

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For most organizations, risk taking is scary. It can be time consuming and unpredictable, with outcomes that aren’t always going to be positive.

But sometimes, the right risk moves your company to an industry-leading position.

Furthermore, as attorney and writer Van Thompson reminds his readers in a column for AZ Central, “not taking a risk can kill a business before it gets off the ground.”

Encouraging employees to take appropriate risks in the real world is a challenge but there are multiple steps that managers often take to make it happen.

They impart repeated face to face reminders that their company welcomes unconventional approaches to issues. They also encourage employees to bond with each other in lunchrooms, at meetings, and through shared experiences.

If building a risk-taking culture is challenging in the real world, it can be even harder to build that level of psychological safety for a remote team. However, there are some things managers of remote teams can do to help.

Encourage your virtual team to make authentic connections

When a workplace culture centers around collaboration and inclusivity, employees will feel a sense of community and comfort with their colleagues. When team members feel comfortable with each other, they trust that if they risk and fail they’ll have support rather than criticism and negative consequences. They also know each other well enough to be able to bring out the best in one another.

How can this happen virtually? Start by encouraging employees to share information in chat messages that goes beyond the work that they’re doing,

Tools like Swirl can help. In it, employees can fill out detailed profiles with unconventional elements you don’t see anywhere else. These questions help employees more deeply express who they are. It can also help them find what they have in common so they’ll enjoy working together more.

It is a secure space for building a team that can share their authentic selves with one another.

If your employees are slow to get started, try to model what you’re looking for. Lead the way. Create your own profile. Share something about yourself in a conversation.

As a manager, you’ll also want to promote an attitude of openness, where people can be themselves without judgment and bond with each other.

Encourage, support, and even normalize risk

Real-world organizations that have successfully encouraged risk taking have found a way to encourage and even normalize it within their workforce.

In many of these companies, their environment and culture support looking at success like a lab where experiments are expected in order to eventually get the outcome you want. A project isn’t something you have to get right the first time.

There are ways to create this same culture in a virtual workspace.

In this effort, words and messages count for a lot. Virtual managers can frequently talk openly about risk taking, what it looks like, and what it means. They can also talk about what failure means to them, diminishing its stigma.

This is similar to how Ariana Huffington has encouraged entrepreneurs to move past their fear of failure. She reminds them that “failure is not the opposite of success, it is the stepping stone to success.”

Use message boards and chat platforms to remind everyone that risk taking is a goal that is supported and encouraged. Say it plainly.

Then follow up by sharing stories and experiences about the behaviors you’re looking to see. Do this frequently and virtual employees will get the message.

Create concrete risk-connected goals that integrate with other work processes.

Make risk taking concrete and it is more likely to happen.

Set goals, standards, and processes that your employees should meet. Use messaging and chats to communicate about them.

What does this look like? One way is to set an expectation that each employee or a team is responsible for coming up with a predesignated number of new ways to achieve a goal.

Establish these numbers, communicate them virtually, and then follow up.

With this approach, you may see that the right goals, when supported by a foundation of teamwork and culture that normalizes risks, will bring results.

You’ll find that your virtual team can find a new way of doing things that puts you ahead of your competitors. They’ll be happier working together and will be on board with helping you build outstanding products for the long term.

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Munir Pathak
tryswirl

Industrial engineer, epidemiologist, biostatistician, data scientist. Passionate about building technology for social impact. Founder @tryswirl tryswirl.com